Water → HCID 136348385, compound

HRID 869503Notes

Reaction equation

HRID 869503 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([CH2:14][C:15]3[CH:38]=[CH:37][C:18]4/[C:19](=[C:29](\[C:31]5[NH:32][O:33][C:34](=[O:36])[N:35]=5)/[CH3:30])/[C:20]5[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=5[O:22][CH2:23][C:17]=4[CH:16]=3)=[C:9]([C:11]([NH2:13])=O)[N:10]=[C:4]2[CH:3]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>C1COCC1>[C:11]([C:9]1[N:10]=[C:4]2[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][N:5]2[C:8]=1[CH2:14][C:15]1[CH:38]=[CH:37][C:18]2/[C:19](=[C:29](\[C:31]3[NH:35][C:34](=[O:36])[O:33][N:32]=3)/[CH3:30])/[C:20]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:21]=3[O:22][CH2:23][C:17]=2[CH:16]=1)#[N:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 9845Trifluoroacetic anhydride2×HCID 178435249HCID 178435249, compound

Product 1

HCID 136348385HCID 136348385, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[step 2] (E)-7-fluoro-3-({3-fluoro-11-[1-(5-oxo-1,2,4-oxadiazol-3-yl)ethylidene]dibenzo[b,e]oxepin-8-yl}methyl)imidazo[1,2-a]pyridine-2-carboxamide (113 mg, 0.22 mmol) obtained in step 1 was dissolved in THF (2 mL), triethylamine (67 mg, 0.66 mmol) and trifluoroacetic anhydride (138 mg, 0.66 mmol) were added and the mixture was stirred at room temperature for 2 hr. Furthermore, triethylamine (89 mg, 0.88 mmol) and trifluoroacetic anhydride (184 mg, 0.88 mmol) were added, and the mixture was stirred at room temperature for 8 hr. Water was added to the reaction mixture, and the mixture was extracted 3 times with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=9/1 v/v) to give the title compound (compound 14i) (15 mg, 14%).

Workup

  1. stirringthe mixture was stirred at room temperature for 8 hr
  2. extractionthe mixture was extracted 3 times with chloroform
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=9/1 v/v)

Sources & evidence

ORD record
ord-565c2814fd1d45aab061392f20dfefbd
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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